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从红树林内生真菌 Hypomontagnella monticulosa YX702 中分离得到细胞毒性四氢呋喃酸衍生物。

Cytotoxic tetronic acid derivatives from the mangrove endophytic fungus Hypomontagnella monticulosa YX702.

机构信息

Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology, the NMPA and State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou 511436, China.

Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology, the NMPA and State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou 511436, China.

出版信息

Fitoterapia. 2023 Oct;170:105656. doi: 10.1016/j.fitote.2023.105656. Epub 2023 Aug 19.

DOI:10.1016/j.fitote.2023.105656
PMID:37604245
Abstract

Three new tetronic acid derivatives, nodulisporacid A ethyl ester (3), isosporothric acid methyl ester (4), and (R)-3-(methoxycarbonyl)-2-methyleneundecanoic acid (5) were isolated from mangrove endophytic fungus Hypomontagnella monticulosa YX702, together with three known analogues nodulisporacid A (1), nodulisporacid A methyl ester (2), and dihydrosporothriolide (6). The structures of these new compounds were elucidated by analysis of NMR and HR-ESI-MS spectroscopic data. In addition, the absolute configuration of nodulisporacid A (1) was confirmed by single-crystal X-ray diffraction for the first time. Subsequently, the absolute configuration of compounds 2 and 3 were determined by chemical derivatization of nodulisporacid A (1). The absolute configuration of compound 4 and 5 were established by TDDFT ECD calculations. Compounds 1 and 2 exhibited cytotoxic activities against A549 and Hela cancer cell lines with the IC values between 5.64 and 8.14 μM.

摘要

从红树林内生真菌 Hypomontagnella monticulosa YX702 中分离得到三个新的四氢酸衍生物:结节孢菌素 A 乙酯(3)、异孢菌素酸甲酯(4)和(R)-3-(甲氧基羰基)-2-亚甲基十一烷酸(5),以及三个已知类似物:结节孢菌素 A(1)、结节孢菌素 A 甲酯(2)和二氢孢子内酯(6)。这些新化合物的结构通过 NMR 和 HR-ESI-MS 光谱数据分析进行了阐明。此外,结节孢菌素 A(1)的绝对构型首次通过单晶 X 射线衍射得到证实。随后,通过结节孢菌素 A(1)的化学衍生化确定了化合物 2 和 3 的绝对构型。通过 TDDFT ECD 计算确定了化合物 4 和 5 的绝对构型。化合物 1 和 2 对 A549 和 Hela 癌细胞系表现出细胞毒性活性,IC 值在 5.64 和 8.14 μM 之间。

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